Motor fuel containing synergistic octane appreciator



United States atent 3,082,070 Patented Mar. 19, 1963 3,082,070 MOTORFUEL CONTAINING SYNERGISTIC OCTANE APPRECIATOR George W. Eckert,Wappingers Falls, N.Y., assignor to Texaco Inc., a corporation ofDelaware N Drawing. Filed Jan. 28, 1959, Ser. No. 789,529 18 Claims.(Cl. 4453) This invention relates to a hydrocarbon fuel composition ofhigh octane rating. More specifically, it involves the discovery thatthe octane rating of leaded gasoline fuels is substantially improved bythe addition of synergistic additive mixtures of hydrocarbylmonocarboxylic acids or tertiary alkyl esters thereof with low molecularweight aliphatic alcohols.

The recent increases in compression ratios of automobile engines haveplaced a severe strain on petroleum refiners to produce fuels having theoctane rating demanded by these engines. Premium fuels at the presenttime have research octane ratings between 97 and 100 and it has beenpredicted that premium fuels will require octane ratings between 105 and110 five years from now in order to satisfy the octane requirements ofthe high compression automotive engines predicted for that date. Inorder to produce premium fuels of octane ratings of 97 and above, it hasbeen necessary for refiners to rely heavily on catalytic refiningoperations such as fluid catalytic cracking, catalytic reforming,alkylation and catalytic isomerization.

Catalytic cracking and catalytic reforming, which are the most Widelyused refining operations in the production or high octane fuels, producesubstantial quantities of aromatics; catalytic cracking also produces asubstantial amount of olefins. It is well known that olefins andaromatics, although possessing high octane ratings have a poorerresponse to organo-lead compounds such as tetraethyl lead than saturatedaliphatic gasoline components. Accordingly, as the aromatic and olefiniccontent of the gasolines have increased to meet the octane levels required by modern automotive high compression engines, the lead responseof the resulting fuels has diminished. Stated another way, the octaneincrement obtainable by the addition of an organo-lead compounddecreases as the aromatic and olefin contents of the base fuel increase.

In my commonly assigned copending application Serial No. 689,466, filedOctober 11, 1957, it is disclosed that hydrocarbyl monocarboxylic acidssubstantially raise the octane rating of a motor fuel containing anorgano-lead anti-knock agent and a substantial concentration of highoctane components which may be aromatic hydrocarbons, olefinichydrocarbons or mixtures thereof. In another commonly-assigned copendingapplication Serial No. 699,944, filed December 2, 1957 in the names ofGeorge W. Eckert, Howard V. Hess and Edwin C. Knowles, it is disclosedthat t-alkyl esters of hydrocarbyl monocarboxylic acids have a similaroctane appreciating action on leaded fuels of this composition.

Low molecular weight aliphatic alcohols have long been used ascomponents of gasoline fuels, methyl, ethyl, isopropyl and butylalcohols are known to possess high octane ratings and their use per seand as components of high octane gasoline has been suggested in manypatents and publications. The recommended concentration of aliphaticalcohol for improving the octane rating of gasoline blends ranges fromabout 5 to about 50 or more volume percent of the total fuel. The use ofsmall concentrations of low molecular weight aliphatic alcohols, thatis, of the order of 0.2 to 2.0 volume percent has been widely practicedin recent years to impart anti-icing, antistalling properties togasoline.

The subject invention involves the discovery that the octane rating ofleaded motor fuels containing a substantial concentration of high octanearomatic and/or olefinic components is markedly improved by the additionof a small amount of a mixture of a hydrocarbyl monocarboxylic acid or atertiary alkyl ester thereof and an aliphatic alcohol.

The high octane hydrocarbon motor fuels of this invention comprise highoctane components including a substantial concentration of aromatichydrocarbons, olefinic hydrocarbons or mixtures thereof, an organo-leadantiknock agent, a hydrocarbyl monocarboxylic acid or a tertiary alkylester thereof in a concentration of at least 0.1 volume percent and alow molecular weight aliphatic alcohol in a concentration of at least0.2 volume percent of the fuel.

This invention also is directed to a synergistic octane appreciatingmixture comprising 1-50 parts of hydrocarbyl monocarboxylic acid, atertiary alkyl ester or mixture thereof and 2-100 parts of aliphaticalcohol for use in leaded fuels containing the prescribed aromaticand/or olefin content. This synergistic octane appreciating additiveadvantageously comprises 2-15 parts of monocarboxylic acid or t-alkylester and 5-20 parts low molecular weight aliphatic alcohol.

The afore-identified copending applications disclose that the action ofmonocarboxylic acid-s and t-alkyl esters in raising the octane rating ofgasoline is. characterized by several unusual features. First, theseagents appear to be ineffective in raising the octane rating ofgasolines unless an organo-lead anti-knock agent, normally tertaethyllead, is a component of the gasoline mixture. Second equalconcentrations of these agents cause a greater octane improvement abovethe 100 octane level than below the 100 octane level. Third,monocarboxylic acids and talkyl esters appear to have little effect onthe octane rating of a gasoline consisting essentially of saturatedaliphatic hydrocarbons even though an organo-lead anti-knock agent ispresent. The synergistic octane appreciators comprising a monocarboxylicacid or a tertiary alkyl ester and an aliphatic alcohol is characterizedby the same properties and accordingly is effective in a base fuelcontaining an organo-lead anti-knock agent and a substantialconcentration of aromatics and/or olefins.

The novel fuel compositions of this invention have a minimumconcentration of aromatic and/ or olefin components of about 10 volumepercent. The aromatic and/or olefin components of the motor fuel of theinvention can constitute as high as 100 volume percent thereof butusually fall between 20 and volume percent. A minimum 10 percentconcentration appears tobe necessary for the synergistic action of amonocarboxylic acid or its t-alkyl ester and an aliphatic alcohol inimproving the octane rating.

The aromatic components of the motor fuel of the invention are generallysupplied by catalytic reforming or catalytic cracking operations.Catalytic reformate is particularly high in aromatics. The olefincomponents of the motor fuel of the invent-ion are derived either fromthermal cracking, catalytic cracking or polymerization.

The organo-lead reagent necessary for the action of the synergisticoctane improver is a tctraalkyl lead compound of the class known topossess anti-knock action. Tetraethyl lead is practically universallyused as an anti-knock agent but other .tetraalkyl lead compounds such astetramethyl lead, tetrabutyl lead, tetraamyl lead, tetrapropyl lead,etc. are known to possess anti-knock properties and may be used in thefuel compositions of the invention.

The tetraethyl lead mixtures commercially available for automotive usecontain an ethylene chloride-ethylene bromide mixture as a scavenger forremoving lead from the combustion chamber in the form of volatile leadhalides. Tetraethyl lead fluid denotes the commercial product whichcomprises tetraethyl lead, ethylene chloride and ethylene bromide, thelatter two reagents being present in 1.0 theory and 0.5 theory,respectively, theory denoting the stoichiometric amount required forreaction with the lead content of the tetraethyl lead.

The organo-lead reagent is present in the fuel compositions of theinvention in concentrations between 0.5 ml. per gallon up to thestatutory limit of organo lead reagent concentration which, at thepresent time, is 3 ml. per gallon in the case of automotive fuel and 4.6ml. per gallon in the case of aviation fuel. The usual concentration oftetraethyl lead is between 1 and 3 ml. per gallon in automotive gasolineand 2-4.6 ml. per gallon in aviation gasoline.

The monocarboxylic acid or ester component of the synergistic additiveof this invention has the general formula: RCOOR' wherein R is hydrogenor a hydrocarbyl radical containing 129 carbon atoms and R is H or atertiary alkyl group containing 4-18 carbon atoms. in the above generalformula, R is advantageously an aliphatic, cycloaliphatic, or arylradical containing 1-8 :arbon atoms; if R is a t-alkyl group itadvantageously :ontains 4-12 carbon atoms.

Hydrocarbyl monocarboxylic acids which form synergistic octaneappreciators with aliphatic alcohols are the following: acetic acid,formic acid, propionic acid, 2- :thylhexanoic acid, lauric acid, stearicacid, 2-ethylbutyric acid, cumic acid, benzoic acid, cyclohexanecarboxylic acid, oleic acid and mixtures thereof. Particularly preferredacids for use in the synergistic octane appreciator at this inventionare acetic acid, Z-ethylhexanoic acid, propionic acid, benzoic acid,cyclohexane carboxylic acid and hexanoic acid.

Tertiary alkyl esters effective as synergistic octane ap- Jreciatorswith aliphatic alcohols in the fuel compositions 3f the invention arethe following: t-butyl acetate, tabutyl formate, t-amyl propionate,t-arnyl caproate, t-amyl heptanoate, t-octyl pelargonate, t-octylcaprate, t-hutyl lautate, t-buytl myristate, t-amyl palmitate, t-nonylstearate, ;-amyl behenate, t-dodecyl :butyrate, t-amyl hexanoate,:-dodecyl o-cumate, t-dodecyl benzoate, t-amyl cyclo- 1exanecar-boxylate, t-octyl cinnarnate, t-amyl phenyl ace- Late, t-butyloleate, t-butyl ester of Snodotte acids (byirogenated fish oil acidscomprising mainly C to C acids) and t-butyl esters of coconut fattyacids (comprislng mainly a mixture of C to C fatty acids).

The preferred tertiary alkyl esters used in the fuel :ompositions of theinvention are derived from aliphatic and aromatic monocarboxylic acidscontaining 1-9 carbon atoms and from a tertiary alkyl radical containing4-12 :arbon atoms. Preferred tertiary alkyl esters are t-butylZ-ethylhexanoate, t-butyl benzoate, t-amyl acetate, t-amyl propionate,t-octyl benzoate, t-butyl hexanoate, t-dodecyl sexanoate, tabutylacetate and t-butyl propionate.

The monocarboxylic acid or t-alkyl ester must be present in the leadedaromatic and/or olefin-containing :ompositions of the invention in aminimum concentration at 0.1 volume percent before a synergistic octaneappreziation is realized. With acid or ester concentrations below 0.1volume percent, neither octane improvement per se nor synergistic actionwith alcohols is obtained in leaded gasoline of prescribed composition.The preferred :oncentration of acid or ester in the synergistic additivefalls between 0.2 and 1.5 volume percent with maximum results generallybeing obtained at a concentration level If about 0.75 volume percent.Although acid or ester :oncentrations as high as 5 volume percent can bein- :orporated in the fuel compositions, economic considera- :ionspreclude the use of such high concentrations. In addition, it appearsthere is a fall-otf in octane improvenent after acid or esterconcentration exceeds about 1.5 lolume percent.

The aliphatic alcohol component of the synergistic anti- :nock additiveof this invention has the general formula: H wherein R is an aliphatichydrocarby'l radical conaining l-10 carbon atoms. The preferred alcoholsfor 4 use in the synergistic anti-knock additive of the inventioncontain l-6 carbon atoms since the lower alcohols not only display amaximum synergistic octane appreciating action with the t-alkyl estersbut they are effective antiicing agents. Examples of alcohols whichreact synergistically with t-alkyl esters are methyl alcohol, ethylalcohol, isopropyl alcohol, n-propyl alcohol, isobutyl alcohol,secondary butyl alcohol, tabutyl alcohol, isoamyl alcohol, n-hexylalcohol, 2-ethylhexanol, isooctyl alcohol and t-am-yl alcohol.

Although minimum concentration of alcohol for synergistic octaneimprovement is set at 0.2 volume percent, the preferred alcoholconcentration employed in the synergistic anti-knock additive of theinvention falls between about 0.5 and 2.0 volume percent. Although ithas been found that concentrations as high as 10 volume percent alcoholcan be used in synergistic combination with acids or t-alkyl esters,alcohol concentrations above about 3.0 volume percent are uneconomic.

In Table I there is shown a synergistic octane appreciating action ofmixtures of tertiary alkyl esters and methyl alcohol in a gasolinehaving a Research Octane Number (RON) of 105. The base fuel contained 3cc. of tetraethyl lead (TEL) per gallon and comprised approximately 10percent n-butane, 40 percent isobutane-isobutylene alkylate, 10 percentpentenes from fluid catalytically cracked naphtha and 40 percent heavyplatformate. By Fluorescent Indicator Analysis (FIA) the base fuel hadan aromatic content of approximately 35 percent and an olefin content ofapproximately 6 percent; its 'IBP was and its end point was 367 F.

TABLE I Units Improvement in RON With Mixtures of Tertiary Alkyl Estersand Methyl Alcohols in Octane Gasoline Concentration of methyl alcohol,volume percent Ester concentration The data in Table I show clearly thesynergistic octane appreciating action of mixtures of methyl alcohol andt-alkyl esters in leaded high octane gasoline having the prescribedaromatic and/or olefin content. It will be noted that methyl alcohol inamounts up to about 2.0 volume percent, has substantially no octaneappreciating action. As the concentration of methyl alcohol increasesfrom 3 to about 7.5 volume percent the octane appreciating action of thealcohol alone rises from about 1 RON unit to 3 RON units. It issignificant that a synergistic octane appreciating action is obtainedwith mixtures of t-alkyl esters and methyl alcohol throughout the wholerange of alcohol concentration.

The synergistic action of the t-alkyl esters with methyl alcohol isexemplified in Table I by the fact that a mixture of 0.75 percentt-butyl acetate and 1.0 percent methyl alcohol appreciates the octanerating of 105 octane gasoline by 2.5 units whereas only a 1.9 unitimprovement would be expected if the additives acted independently.Similarly, a mixture of 0.75 percent t-butyl acetate and 2.0 percentmethyl alcohol effected a 3.2 unit improvement whereas only a 2.0 unitoctane improvement would have been obtained if the additives actedindependently.

In Table II there is shown the octane appreciating action of t-alkylesters with C to C aliphatic alcohols.

The 105 octane base fuel employed in obtaining the data shown in TableII had the same composition as the base fuel employed.- in Table I.

TABLE II Units Improvement in RON With Mixtures of t-Butyl Esters andAliphatic Alcohols Additive: Increase in RON 0.75% t-butyl acetate 1.80.75% t-butyl propionate 1.7 1.0% ethyl alcohol 0.0 1.0% isopropylalcohol 0.0 1.0% t-butyl alcohol 0.0 1.0% sec-butyl alcohol 0.0 1.0%isobutyl alcohol 0.0 1.0% n-butyl alcohol 0.0 2.0% Z-ethylbutanol 0.0

0.75% t-buty1acetate+l.0% ethyl alcohol 2.9 0.75% t-butyl acetate+l.0%isopropyl alcohoL 3.0 [0.75% t-butyl acetate-{4.0% sec-butyl alcohol-2.5 0.75% t-butyl acetate+1.0% isobutyl alcohol 2.8 0.75% t-butylacetate+l.0% n-butyl alcohol"- 2.7 0.75% tbutyl acetate+2.0%2-ethylbutanol 2.6 0.75% t-butyl propionate+1.0% isopropyl alco- 5 hol2. 0.75% t-buty1acetate+l.0% t-butyl alcohoL" 2.

The synergistic action of t-alkyl esters and methyl alcohol in regularand premium gasolines is shown in Table III. Base Fuel A was a premiumgrade gasoline containing 3 cc. of TEL per gallon and comprisingapproximately 50% saturates, 41% aromatics and 9% olefiris by FIAmethod; base fuel A which had in IBP of 89 F. and an end point of 372 F.had a leaded RON of 100.7.

Base fuel B Was a regular grade gasoline containing 3 cc. of TEL pergallon and comprising approximately 56% saturates, 22% olefins and 22%aromatics by PIA method; base fuel B which had an IBP of 92 F. and anend point of 367 F., had a leaded RON of about 93.0.

TABLE III Units Improvement in RON With Mixtures of t-Butyl Acetate andMethyl Alcohol Increase in RON The data in Table 111 show clearly thesynergistic octane appreciating action of mixtures of t-butyl acetateand methyl alcohol in regular and premium .grade gasoline. "It issignificant that a greater increase in RON is obtained with thesynergistic mixture in the premium fuel than in the regular fuel.Comparison with the results shown in Tables I and II indicate that aneven greater increase in RON is obtained with the synergistic mixturewhen the octane level reaches 105. This property of the synergisticmixture is akin to the action of monocarboxylic acids and its t-alkylesters as disclosed in the af-ore-identified copending applicationsSerial Nos. 689,466 and 699,944.

In Table IV there is shown the synergistic octane appreciating action ofmixtures of hydrocarbyl monocarboxylic acids and alcohols in the 105octane base fuel employed in Table I.

y 6 TABLE IV Units Improvement in RON With Mixtures of Monoca-rboxylicAcids and Aliphatic Alcohols in Octane Gasoline Additive: Increase inRO-N 1.0% methyl alcohol 0.1 1.0% isopropyl alcohol 0.( 1.0% t-butylalcohol 0C 0.5% 2-ethylhexanoic acid 2.7 0.3% propionic acid 2.6 0.5%benzoic acid 3.4 0.5 Z-ethylhexanoic acid+1.0% methyl alcohol 3.5 0.3%propionic acid|1.0% methyl alcohol 3.] 0.3% propionic acid|1.0%isopropyl alcohoLo 4.2 0.5 benzoic acid+1.0% t-butyl alcohol 3.8

The data in Table IV demonstrate the synergistic octane appreciatingaction of mixtures of hydrocarbyl monocarboxylic acids and aliphaticalcohols in a leaded gasoline containing the prescribed aromatic and/ orolefin content.

This invention is an important advance in the technology of high octanefuels since it provides means whereby the significant octaneappreciating action of t-alkyl esters and hydrocarbyl monocanboxylicacids on leaded fuels of prescribed compositions is significantlyenhanced using readily available reasonably priced materials which arealready widely used as gasoline components for their anti-icingfunction. It is noteworthy that the fuels of this invention containing asynergistic octane appreciating mixture of a hydrocarbyl monocarboxylicacid or a talkyl ester thereof with a low molecular weight aliphaticalcohol are characterized by the excellent anti-stalling and anti-icingproperties as a result of the presence there in of low molecular weightalcohols.

The selectivity of the synergistic octane appreciating action ofmixtures of 'taalkyl esters 'with alcohols was demonstrated by the factthat mixtures comprising 0.75 percent t-bu tyl acetate and various otheroxygenated hydnocarbon derivatives gave the same or poorer octaneappreciation than that obtained with 0.75 percent t-butyl acetate alone.Table III lists the oxygenated hydrocarbon-s which display nosynergistic octane appreciating action with t-butyl acetate.

Obviously, many modifications and variations of the invention ashereinbefore set forth may be made without departing from the spirit andscope thereof and, therefore, only such limitations should be imposed asare indicated in the appended claims.

I claim:

1. A hydrocarbon fuel in the gasoline boiling range containing an alkyllead anti-knock agent, high octane components selected from the groupconsisting of olefinic hydrocarbons, aromatic hydrocarbons and mixturesthereof in a concentration of at least 10 volume percent 01 said fueland a synergistic additive combination of (1) an acidic compoundselected from the group consisting of hydrocarbyl monocarboxylic acidscontaining 1 to 30 carbon atoms, their tertiary alkyl esters andmixtures thereof and (2) a low molecular weight aliphatic alcohol of thegeneral formula: ROl-I wherein R is an aliphatic hydrocarbyl radicalcontaining 1-10 carbon atoms, said acidic compound being present in aconcentration between 0.1 and 5.0 volume percent of said fuel and saidalcohol being present in a concentration between 0.2 and 5.0 volumepercent of said fuel said combination effecting a substantialimprovement of the octane rating of said iorgano-lead-containinghydrocarbon fuel.

2. A hydrocarbon fuel according to claim 1 in which said acidic compoundhas the general formula: RCOOR' wherein R is selected from the groupconsisting of hydrogen and hydrocarbyl radicals containing 1-29 carbonatoms, and R is selected from the group consisting of hydrogen and at-al kyl group containing 4-18 carbon atoms.

3. A hydrocarbon fuel according to claim 1 in which said alkyl leadanti-knock agent is present in a concentration between 0.5 and 4.6 cc.per gallon.

4. A hydrocarbon fuel in the gasoline boiling range containing an alkyllead anti-knock agent in a concentration of at least 0.5 cc. per gallon,high octane components selected from the group consisting of olcfinichydrocarbons, aromatic hydrocarbons, and mixtures thereof, in aconcentration of at least 10 volume percent of said fuel, a synergisticadditive combination of (1) an acidic compound having the generalformula: RCOOR' wherein R is a hydrocarbyl radical containing 1-8 carbonatoms and R is selected from the group consisting of hydrogen and at-a-lkyl group containing 4-12 carbon atoms, and (2) a low molecularweight aliphatic alcohol having the general formula: ROI-I wherein R isan aliphatic hydrocarbyl radical containing 1-6 carbon atoms, saidacidic compound being present in a concentration between 0.1 and 5 .0volume percent and said alcohol being present in a concentration between0.2 and 5.0 volume percent.

5. A hydrocarbon fuel according to claim 4 in which said acidic compoundis present in a concentration of 0.2 to 1.5 volume percent and saidalcohol is present in a concentration of 0.5 to 2.0 volume percent.

6. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises t-butyl acetate and methyl alcohol.

7. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises -t-butyl propionate and methyl alcohol.

8. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises t-butyl acetate and isopropyl alcohol.

9. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises t-butyl acetate and ethyl alcohol.

10. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises t-amyl acetate and methyl alcohol.

11. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises t-butyl acetate and t-butyl alcohol.

12. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises propionic acid and methyl alcohol.

13. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises propionic acid and isopropyl alcohol.

14. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises 2-ethylhexanoic acid and methyl alcohol.

15. A hydrocarbon fuel according to claim 4 in which said additivecombination comprises benzoic acid and t-butyl alcohol.

16. A synergistic octane appreciating additive for leaded fuelscontaining a substantial concentration of high octane componentsselected from the group consisting of aromatic and olefinic hydrocarbonsand mixtures thereof consisting of 1-50' parts by volume of an acidiccompound having the general formula: RCOO-R wherein R is selected fromthe group consisting of hydrogen and hydrocarbyl radicals containing1-29 carbon atoms and R is selected from the group consisting ofhydrogen and a t-alkyl group containing 4-18 carbon atoms and 2-100parts by volume of a low molecular weight aliphatic alcohol of thegeneral formula: ROI-I wherein R is an aliphatic hydrocarbyl radicalcontaining 1-10 carbon atoms.

17. A synergistic additive combination according to claim 16 comprising2 to 15 parts by volume of said acidic compound and 5 to 20 parts byvolume of said alcohol.

18. A synergistic octan'e appreciating additive according to claim 16 inwhich said acidic compound has the general formula: RCOOR' wherein R isa hydrocarbyl radical containing 1-8 carbon atoms and R is selected fromthe group consisting of hydrogen and a t-alkyl group containing 4-12carbon atoms and said alcohol has the general formula: ROI-I wherein Ris an aliphatic hydrocarbyl radical containing 1-6 carbon atoms.

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16. A SYNERGISTIC OCTANE APPRECIATING ADDITIVE FOR LEADED FUELSCONTAINING A SUBSTANTIAL CONCENTRATION OF HIGH OCTANE COMPONENTSSELECTED FROM THE GROUP CONSISTING OF AROMATIC AND OLEFINIC HYDROCARBONSAND MIXTURES THEREOF CONSISTING OF 1-50 PARTS BY VOLUME OF AN ACIDICCOMPOUND HAVING THE GENERAL FORMULA: RCOOR'' WHEREIN R IS SELECTED FROMTHE GROUP CONSISTING OF HYDROGEN AND HYDROCARBYL RADICALS CONTAINING1-29 CARBON ATOMS AND R'' IS SELECTED FROM THE GROUP CONSISTING OFHYDROGEN AND A T-ALKYL GROUP CONTAINING 4-18 CARBON ATOMS AND 2-100PARTS BU VOLUME OF A LOW MOLECULAR WEIGHT ALIPHATIC ALCOHOL OF THEGENERAL FORMULA: ROH WHEREIN R IS ALIPHATIC HYDROCARBYL RADICALCONTAINING 1-10 CARBON ATOMS.